Divergent access to α-carbonyl-α′-vinyl sulfoxonium ylides and polysubstituted furans from β-ketosulfoxonium ylides and ynone-esters

TitleDivergent access to α-carbonyl-α′-vinyl sulfoxonium ylides and polysubstituted furans from β-ketosulfoxonium ylides and ynone-esters
Publication TypeJournal Article
Year of Publication2025
AuthorsIngale, SR, Sahu, MRanjan, Borade, BR, Gamidi, RKrishna, Kontham, R
JournalJournal of Organic Chemistry
Volume90
Issue18
Pagination6186-6207
Date PublishedAPR
Type of ArticleArticle
ISSN0022-3263
Abstract

Here, we describe the synthesis of novel alpha-carbonyl-alpha `-vinyl sulfoxonium ylides under ambient, catalyst-free, and additive-free conditions, demonstrating broad substrate scope and scalability using beta-ketosulfoxonium ylides and alpha-ynone-esters. Furthermore, these ylides serve as versatile intermediates for the synthesis of highly substituted furans via Br & oslash;nsted acid (p-TsOH) catalysis at 130 degrees C. This approach offers key advantages, including wide substrate compatibility, divergent product formation from common precursors, gram-scale feasibility, and good to excellent yields.

DOI10.1021/acs.joc.5c00245
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.2

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Database: 
Web of Science (WoS)

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